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741825

Sigma-Aldrich

XPhos Pd G2

98%

Synonym(s):

2nd Generation XPhos Precatalyst, Chloro(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II), X-Phos aminobiphenyl palladium chloride precatalyst, XPhos-Pd-G2

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About This Item

Empirical Formula (Hill Notation):
C45H59ClNPPd
CAS Number:
1310584-14-5
Molecular Weight:
786.80
UNSPSC Code:
12161600
PubChem Substance ID:
329765534
NACRES:
NA.22

Quality Level

100

Assay

98%

form

solid

feature

generation 2

reaction suitability

core: palladium
reaction type: Buchwald-Hartwig Cross Coupling Reaction
reaction type: Heck Reaction
reaction type: Hiyama Coupling
reaction type: Negishi Coupling
reaction type: Sonogashira Coupling
reaction type: Stille Coupling
reaction type: Suzuki-Miyaura Coupling
reagent type: catalyst
reaction type: Cross Couplings

mp

202-210 °C

functional group

phosphine

SMILES string

Nc1ccccc1-c2ccccc2[Pd]Cl.Nc3ccccc3-c4ccccc4[Pd]Cl.CC(C)c5cc(C(C)C)c(-c6cccc(c6)P(C7CCCCC7)C8CCCCC8)c(c5)C(C)C.CC(C)c9cc(C(C)C)c(c(c9)C(C)C)-c%10ccccc%10P(C%11CCCCC%11)C%12CCCCC%12

InChI

1S/2C33H49P.2C12H10N.2ClH.2Pd/c1-23(2)27-21-31(24(3)4)33(32(22-27)25(5)6)26-14-13-19-30(20-26)34(28-15-9-7-10-16-28)29-17-11-8-12-18-29;1-23(2)26-21-30(24(3)4)33(31(22-26)25(5)6)29-19-13-14-20-32(29)34(27-15-9-7-10-16-27)28-17-11-8-12-18-28;2*13-12-9-5-4-8-11(12)10-6-2-1-3-7-10;;;;/h13-14,19-25,28-29H,7-12,15-18H2,1-6H3;13-14,19-25,27-28H,7-12,15-18H2,1-6H3;2*1-6,8-9H,13H2;2*1H;;/q;;;;;;2*+1/p-2

InChI key

HMRJFNBZAWHTGN-UHFFFAOYSA-L

General description

XPhos Pd G2 is a bulky monodentate biaryl ligand. It is a Buchwald′s 2nd generation preformed catalyst. It undergoes rapid reductive elimination to form a reactive, monoligated Pd(0) species.

Application

2nd Generation Buchwald Precatalysts

  • Widely used for Suzuki-Miyaura cross-coupling reactions
XPhos Pd G2 was employed as catalyst in the following reactions:
  • Palladium-catalyzed Suzuki-Miyaura coupling reactions of potassium organotrifluoroborates and sulfamates.
  • Suzuki-Miyaura cross-coupling reactions of sensitive aryl and heteroarylboronic acids.
  • Synthesis of potassium Boc-protected secondary aminomethyltrifluoroborates, via Suzuki-Miyaura cross-coupling reaction.
For small scale and high throughput uses, product is also available as ChemBeads (927775)

related product

Product No.
Description
Pricing

903728

DavePhos Pd G2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
SHBN0273
MKCQ3097
SHBM4793
SHBM2890
SHBL9642

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Gary A Molander et al.
Organic letters, 15(10), 2534-2537 (2013-05-08)
Sulfamates were studied as the electrophilic partners in the palladium-catalyzed Suzuki-Miyaura cross-coupling reaction with potassium Boc-protected primary and secondary aminomethyltrifluoroborates. A broad range of substrates was successfully coupled to provide the desired products. Complex molecules containing a new carbon-carbon bond
Gary A Molander et al.
Organic letters, 14(17), 4458-4461 (2012-08-31)
Seven potassium Boc-protected secondary aminomethyltrifluoroborates were prepared in a standardized two-step process. The Suzuki-Miyaura cross-coupling reaction was studied with this new class of nucleophiles, and a large variety of aryl and hetaryl chlorides provided the desired products in good to
Gary A Molander et al.
The Journal of organic chemistry, 78(8), 4123-4131 (2013-04-11)
A method has been developed for the Pd-catalyzed synthesis of α-(hetero)aryl esters and amides through a Suzuki-Miyaura cross-coupling reaction. This method avoids the use of strong base, does not necessitate inert or low temperature formation of reagents, and does not

Articles

Heck Reaction

The Heck reaction is the palladium catalyzed cross-coupling reaction between alkenes and aryl or vinyl halides (or triflates) to afford substituted alkenes.

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